WO1999007676A1 - Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides - Google Patents

Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides Download PDF

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Publication number
WO1999007676A1
WO1999007676A1 PCT/EP1998/004648 EP9804648W WO9907676A1 WO 1999007676 A1 WO1999007676 A1 WO 1999007676A1 EP 9804648 W EP9804648 W EP 9804648W WO 9907676 A1 WO9907676 A1 WO 9907676A1
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Prior art keywords
formula
lithium
compounds
perfluoroalkane
perfluoroalkylsulfonyl
Prior art date
Application number
PCT/EP1998/004648
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German (de)
English (en)
Inventor
Udo Heider
Volker Hilarius
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Merck Patent Gmbh
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Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to EP98943778A priority Critical patent/EP1001931A1/fr
Priority to JP2000506180A priority patent/JP2001512714A/ja
Priority to KR1020007001199A priority patent/KR20010022605A/ko
Publication of WO1999007676A1 publication Critical patent/WO1999007676A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0568—Liquid materials characterised by the solutes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • PERFLU0RALKAN-1-SULF0NYL (PERFLUORALKYLSULFONYL) IMID-N-SULFONYL CONTAINING METHANIDES, IMIDES AND SULFONATES, AND THEIR USE IN ELECTROLYTE SYSTEMS
  • the invention relates to compounds of the formula I.
  • R and Ri independently of one another RC (S0 2 R F ) 2, N (S0 2 RF), O, mean with a counter ion from the group Li, Na, K, Cs, Rb, B ⁇ / 2 , and n is 1, 2 or 3 and x is 1, 2, 3 or 4, processes for their preparation, their use in electrolyte systems as conductive salts in lithium batteries, and electrolytes for lithium batteries containing compounds of the general formula (I), but also secondary lithium batteries which corresponding electrolytes contain.
  • Lithium compounds such as e.g. B. Li [F 3 CS03] (lithium triflate) are known, which are easy to display and are therefore also commercially available. Corresponding compounds are unsuitable for use in secondary batteries, however, since they have insufficient conductivity in the typical aprotic solvents used therein (Volkov, OV; Skudin, AM; Ignat'ev, NV; Soviet Electrochemistry, 1992, 28, 1527).
  • lithium tris (trifluoromethylsulfonyl) methanide Li [C (S0 2 CF 3 ) 3]
  • lithium bis (trifluoromethylsulfonyl) imide Li [N (S0 2 CF 3 ) 2 j
  • Electrochemical. Sci. Case Western Reserve Univ., Cleveland, OH, USA Report (1989), GRI-89/0025; Order No. PB89-178768, 214 pp. Avail .: from Geov. Rep. Announce. Index (U.S.) 1989, 89 (12), Abstr. No. 932, 621; A. J. Appleby et al. Cent. Electrochemical. Syyt. Hydrogen Res., Texas A and M Univ. System, College Station, TX, 77843-3402, USA, Morgantown Energy Technol. Cent., [Rep.] DOE / METC (U.S. Dep. Energy), 1991 DOE / METC-91/6120, Proc. Annu. Fuel Cells Contract. Rev. Meet.
  • the object of the invention is therefore to provide suitable lithium salts with a sufficient lithium content, which are corrosion-stable, have an improved cation conductivity compared to known comparable lithium salts and at the same time do not lead to any disadvantageous countervoltage due to opposite anion charges.
  • M is a counter ion from the group Li, Na, K, Cs, Rb, B 1 2 , and
  • Alkane bis (sulfonyl fluoride) a sodium perfluoroalkane-1-sulfonyl fluoride-N-trifluoromethylsulfonylimide of the formula (IV)
  • R F has the meaning given above, produces it and either e) it can react with sodium perfluoalkylsulfonyltrimethylsilylamide of the formula (
  • R F has the meaning given above, or f) converts an equivalent with a dilithiated bis (perfluoroalkylsulfonyl) methane and by suitable ones
  • RF has the meaning given above, produces or g) is reacted with an alkaline lithium salt and by salting with a lithium halide perfluoroalkane-1-sulfonyl (perfluoroalkylsulfonyl) imide-N-sulfonate of the formula (VII)
  • the invention also relates to a process for the preparation of compounds of the formula (I) in which R 1 and R are the same and have the meaning (C (S0 2 RF) 2 , characterized in that a) bis (perfluoroalkylsulfonyl) methane in lithiated an aprotic, organic solvent from the group tetrahydrofuran, 2-methyl tetrahydrofuran and diethyl ether at a temperature of -10 - +50 ° C, preferably at 10 to 25 ° C and with an ⁇ , ⁇ -perfluoroalkane bis (sulfonyl fluoride) of the formula ( VIII) F0 2 S- (CF 2 ) n -S0 2 F (VIII) in a molar ratio of 1: 0.3 to 1: 0.5 at
  • Li 2 [(R F S0 2 ) 2 C-S0 2 - (CF 2 ) n-S0 2 -C (S0 2 R F ) 2] (Xb) are particularly the subject of this invention.
  • di-lithium imide sulfonates of the formula (VII) are also di-lithium imide sulfonates of the formula (VII).
  • Alkaline lithium salts from the group Li 2 C0 3 and LiOH * H 2 O or others are suitable for saponification.
  • the di-lithium imide sulfonates can be obtained by salting with a lithium halide, preferably lithium chloride.
  • the invention thus relates to a process which can be represented by the following scheme using the example of the lithium compounds according to the invention:
  • Process scheme 1 As can be seen from the process scheme given above, the compounds of the formula (III) are prepared in three stages. It has now been found that the first reaction step advantageously does not have to be carried out in liquid ammonia, as described by DesMarteau (DD DesMarteau, M. Witz,
  • Formula (IV) produce new lithium compounds of formula (V). It has been found that with increasing chain length of the ⁇ , ⁇ -perfluoroalkane bis (sulfonyl fluoride) used, the yields of the reaction of compounds of the formula (IV) with compounds of the formula (III) which are carried out decrease. After purification and
  • compounds of the formula (V) are prepared by compounds of the formula (IV) in an aprotic solvent from the group of the cyclic, preferably in pyran (corresponds to ( ⁇ ) - 3-methyltetrahydropyran), at temperatures from 100 to 110 ° C. with compounds of formula (III), which are used in a 10 to 20% excess, are reacted.
  • compounds of formula (IX) are obtained:
  • n 1, 2 or 3.
  • di-potassium salts are prepared therefrom with the aid of alkaline-reacting aqueous potassium ion-containing solutions, preferably a potassium hydroxide solution, and subsequent salting with a lithium halide from the group consisting of LiCl, LiJ and LiBr, preferably lithium chloride , in aprotic organic solvents, such as tetrahydrofuran or 1,3-dioxolane ... di-lithium bisimides of the formula (V).
  • aqueous potassium ion-containing solutions preferably a potassium hydroxide solution
  • a lithium halide from the group consisting of LiCl, LiJ and LiBr, preferably lithium chloride
  • aprotic organic solvents such as tetrahydrofuran or 1,3-dioxolane ... di-lithium bisimides of the formula (V).
  • the process according to the invention also relates, as can be seen from the scheme given above, to the preparation of the new perfluoraikan-1-sulfonyl (perfluoroalkylsulfonyl) imide-n-sulfonylbis (perfluoroalkylsulfonyl) methanides or mixed di-lithium imide Methanides of the general formula (VI).
  • bis (perfluoroalkylsulfonyl) methane is used in a nonpolar, aprotic solvent from the group consisting of tetrahydrofuran and 2-methyltetrahydrofuran with the aid of butyl lithium or methyl lithium in a solvent such as cyclohexane, n-hexane or other cyclic or acyclic hydrocarbons at temperatures of - 10 to 30 ° C, preferably at 10 - 20 ° C, dilithiated.
  • the mixed di-lithium imide methanides of the formula (VI) according to the invention can be prepared. After purification, the desired product is obtained in a yield of about 25 to 35%.
  • the present invention also relates to a process for the preparation of di-alkali imide sulfonates, in particular di-lithium imide sulfonates of the formula (VII). Experiments have shown that these compounds can be prepared by saponification of the corresponding monoanion of the formula (IV). For this purpose, an aqueous solution of an alkaline lithium salt from the group LiOH * H 2 0 and Li 2 C0 3 can be used.
  • This reaction is preferably carried out with a lithium hydroxide solution; namely the monoanion is placed in aqueous solution and the alkaline lithium salt is added in an equimolar to 1.5 times the amount.
  • the saponification takes place at elevated temperature, especially at boiling temperature.
  • activated carbon can be added to the reaction solution to remove impurities.
  • the reaction product can be obtained in a simple manner by removing the water and the di-lithium salt can be obtained therefrom by salting.
  • the reaction product of the saponification is obtained in an aprotic solvent from the group consisting of the ethers tetrahydrofuran and 1,3-dioxolane, preferably tetrahydrofuran added and mixed with an equimolar to 1.5 times the amount of a lithium halide, also dissolved in an aprotic organic solvent, preferably the same one that was used to dissolve the saponification product, and at about 20 to 40 ° C., preferably at room temperature for stirred for some time.
  • the sodium halide that forms precipitates and can be used in a simple manner, e.g. B. by filtration or alternative methods known to those skilled in the art. After removal of the solvent, preferably by vacuum distillation, the desired di-alkali imide sulfonate is obtained as a solid in a yield of at least 98%.
  • M 2 [(F 3 CSO 2 ) 2C-S0 2 - (CF 2 ) n -S0 2 -C (SO 2 CF 3 ) 2 ], (X) wherein M, n and R have the meanings given above, the subject of the invention, and a process for their preparation.
  • Bis (perfluoroalkylsulfonyl) methane is in an aprotic solvent from the group of cyclic ethers, preferably in Tetrahydrofuran added and lithiated with the aid of alkyl lithium, such as butyllithium or methyl lithium, which is prepared in a known manner and is dissolved in hydrocarbon, such as cyclohexane. However, it can also be reacted in a corresponding manner with an alkyl-Mg compound. This lithiation reaction can occur in a
  • the starting materials are used in this reaction in a molar ratio of 1: 0.3 to 1: 0.5.
  • the reaction takes place in a cyclic or acyclic ether, preferably in tetrahydrofuran, at temperatures between 10-50 ° C. Particularly good yields are obtained when working in a temperature range of 25-30 ° C.
  • the product obtained is converted to the corresponding dianion with a cesium salt from the group Cs 2 C03, which is alkaline in solution, and CsOH in aqueous solution and by successive treatment , if necessary after prior purification, such as. B. by recrystallization or by other methods known to those skilled in the art, in an organic solvent from the group of diethyl ether and dibutyl ether, with a mineral acid, preferably hydrochloric acid, and by treatment with an aqueous lithium hydroxide solution in the desired salt, such as. B. in the di-lithium bismethanide of the formula (Xa)
  • the di-lithium bismethanide is released in particular by using equimolar amounts of lithium hydroxide or of his hydrate.
  • the lithium hydroxide can also be used in excess to shift the reaction equilibrium.
  • R F in the compounds according to the invention can represent the fluorine-saturated radicals trifluoromethyl, pentafluoroethyl, i- and n-heptafluoropropyl, i-, n-, t-nonafluorobutyl.
  • lithium salts of the compounds of the general formula (I) a) Li 2 [(F 3 CS0 2 ) 2 C-S0 2 -CF 2 -SOrC (S0 2 CF 3 ) 2 ] b) Li 2 [(F 3 CS ⁇ 2 ) 2 C-S0 2 - (CF 2 ) 2 -S0 2 -C (S0 2 CF 3 ) 2 ] c) Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3-S0 2 -C (S0 2 CF 3 ) 2] d) Li 2 [F 3 CSO 2 N-S0 2 -CF 2 -C (S0 2 CF 3 ) 2 ] e) Li 2 [F 3 CS0 2 N-S0 2 - (CF 2 ) 2 -C (S0 2 CF 3 ) 2 ] f) Li 2 [F 3 CS0 2 N-S0 2 - (CF 2 ) 3 ] f
  • the compounds according to the invention are extremely stable. In dry storage at a temperature of around 100 ° C, no decomposition occurs. Only at significantly higher temperatures above 200 ° C does decomposition appear on the basis of discoloration. But also when stored in solution, such as. B. in organic solvents such as tetrahydrofuran or acetonitrile, no color changes or decomposition products can be detected even after several weeks of storage, for this reason the new compounds according to the invention are particularly suitable as a conductive salt in non-aqueous electrolytes for lithium secondary batteries. Such electrolytes contain, in addition to lithium-organic salts, as are the compounds according to the invention, one or more non-aqueous organic solvents and, if appropriate, further additives.
  • lithium secondary batteries Further details on such electrolytes, their structure and the mode of operation of lithium secondary batteries are known to the person skilled in the relevant art.
  • the compounds according to the invention can be used in complete analogy to lithium compounds known for this application.
  • the compounds of the invention also show an extraordinarily high stability.
  • the corresponding battery cells show excellent properties in terms of capacity and
  • Lithium bismethanides have very good conductivities in aprotic solvents. Furthermore, they contribute to a decrease in the tendency to corrode aluminum current arresters and are themselves stable to decomposition reactions. In detail, these salts have a passivating or protective effect on the aluminum.
  • Compounds of the general formula (I) according to the invention which can be used as conductive salts in both primary and secondary cells can therefore act as surface-active salts in electrolytes.
  • the lithium salts described are particularly well suited for use as conductive salts in electrolytes.
  • the advantageous properties of these salts in this connection depend on the content of lithium in the salts produced.
  • the di-lithium imide sulfonate of formula (VII) has the highest lithium content with 3.91%.
  • this salt can be prepared in very good yields by the process described here. So the saponification and the subsequent salting run almost quantitatively.
  • the compound of the formula (IV) used for its preparation is already obtained in a yield of 90% and more, so that the preparation of these conductive salts per se is associated with very low losses of starting material.
  • HMDS hexamethyldisilazane
  • IR (KBr pellet): v 2960 (m), 2903 (w), 1277 (s), 1251 (vs), 1231 (vs), 1205 (vs), 1171 (s), 1145 (s), 1059 (vs), 989 (m), 840 (vs), 762 (m), 730 (w), 712 (m), 692 (w), 620 (s), 579 (m), 548 (w), 523 (w), 489 (w), 483 (w), 476 (w), 471 (w), 462 (w), 427 (w).
  • the sublimation sump is taken up in 100-150 ml of water, filtered through granular activated carbon and neutralized with potassium hydroxide. After boiling with activated carbon and subsequent filtration, the water is removed in vacuo. The colorless solid is recrystallized from approx. 300 - 400 ml isopropanol. After filtering, the crystals are dried in a high vacuum at 70 ° C.
  • a solution of 15.40 is added to a solution of 100.00 g (182 mmol) of K 2 [F 3 CS0 2 -N-S0 2 -CF 2 - S0 2 -N-S0 2 CF 3 ] in 100 ml of tetrahydrofuran g (364 mmol) lithium chloride in 650 ml tetrahydrofuran. After stirring for 30 minutes, the precipitated potassium chloride is filtered off and the THF is removed in vacuo. The resulting colorless solid is dried under high vacuum ( ⁇ 0.1 Torr) at about 80 ° C.
  • the reaction solution is heated to 60 ° C for two hours.
  • the solvent mixture is then removed.
  • the resulting solid is taken up in 500 ml of 3 molar hydrochloric acid and stirred for about four hours.
  • the solution is then extracted four times with 150 ml of diethyl ether each time. After combining the ether phases and removing the solvent, the unreacted starting materials are distilled off.
  • the remaining sump is dissolved in 500 ml of water and neutralized with approx. 33 g of cesium carbonate.
  • the cesium salt that precipitates is brought into solution by boiling.
  • the solution is then mixed with activated carbon and, after heating for 30 minutes, filtered, the cesium salt which has crystallized out is optionally recrystallized again with water.
  • the salt Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 ) 2 ] has EC / DMC (1: 1; water content of about 10 - 20 ppm) and EC / DEC (1: 1; water content of about 10 - 20 ppm) good stability towards lithium, in the base current
  • Cyclic voltammograms show no signals that could indicate cathodic decomposition.
  • Oxidation stability a) Oxidation on inert platinum electrodes The decomposition potential of the divalent methanide was determined to be 5.3 V versus Li / Li + , regardless of the solvent mixture. This indicates that the solvent is probably already decomposing.
  • Fig. 2. shows a voltammogram measured with an EC / DMC mixture as a solvent.
  • cyclic properties were determined potentiodynamically using cyclic voltammetry (Fig. 3, Tab. 4) and galvanostatically (Tab. 5 and 6). The results are in the range of the salts already examined.
  • Fig. 1 are basic current cyclic voltammetric measurements which are performed using Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 )] (0.58 molal) in DMC / EC (mdcv 279) were carried out, graphically evaluated.
  • the implementation was carried out under the following conditions:
  • Electrode area 0.503 cm 2
  • Measuring arrangement 3 electrode arrangement working electrode V2A stainless steel
  • Electrode area 0.503 cm 2
  • FIG. 3 shows a graphical representation of the lithium deposition by means of cyclovoltaic experiments, using the example of Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 ) 2 ] (0.58 molal) in DMC / EC (mdcv 280).
  • the implementation was carried out under the following conditions:
  • Measuring arrangement 3 electrode arrangement working electrode V2A stainless steel
  • Electrode area 0.503 cm 2
  • Fig. 4 shows the anodic stability of Li 2 [(F 3 CS0 2 ) 2 C-SO 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 ) 2 ] (0.58 molal) in DMC / EC (mdcv 284) on aluminum (electrode area o, 583 cm 2 )
  • Strip current density istrip 1 mA cm 2
  • Strip current density istrip 1 mA / cm 2

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Abstract

L'invention concerne des composés de la formule (I) M2[R1-SO2-(CF2)n-SO2-R]; dans laquelle R et R1 sont indépendants l'un de l'autre, R désignant C(SO2RF)2, N(SO2RF), O, R1 désignant C(SO2RF)2, N(SO2RF), RF désignant (CxF;2x+1), M désignant un contre-ion du groupe comprenant Li, Na, K, Cs, Rb, B1/2, et Mg1/2, Sr1/2, Ba1/2, n valant 1, 2 ou 3 et x valant 1, 2, 3 ou 4. L'invention concerne des procédés permettant de les préparer, leur utilisation dans des systèmes électrolytiques, comme sels conducteurs dans des piles au lithium, ainsi que comme électrolytes pour des piles au lithium contenant des composés de la formule générale (I), mais également des piles au lithium secondaires en soi qui contiennent les électrolytes correspondants.
PCT/EP1998/004648 1997-08-06 1998-07-24 Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides WO1999007676A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP98943778A EP1001931A1 (fr) 1997-08-06 1998-07-24 Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides
JP2000506180A JP2001512714A (ja) 1997-08-06 1998-07-24 ペルフルオロアルカン−１−スルホニル（ペルフルオロアルキルスルホニル）イミド−ｎ−スルホニル−含有メタニド、イミドおよびスルホネート化合物の製造方法およびペルフルオロアルカン−１−ｎ−スルホニルビス（ペルフルオロアルキルスルホニル）メタニド化合物
KR1020007001199A KR20010022605A (ko) 1997-08-06 1998-07-24 퍼플루오로알칸-1-설포닐(퍼플루오로알킬설포닐)이미드-엔-설포닐을 포함하는 메타나이드, 이미드 및 설포네이트, 및퍼플루오로알칸-1-엔-설포닐비스(퍼플루오로알킬설포닐)메타나이드의 제조방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19733948.4 1997-08-06
DE19733948A DE19733948A1 (de) 1997-08-06 1997-08-06 Verfahren zur Herstellung von Perfluoralkan-1-sulfonyl(perfluoralkylsulfonyl) imid-N-sulfonyl enthaltende Methanide, Imide und Sulfonate, und Perfluoralkan-1-N-(sulfonylbis(perfluoralkylsulfonyl)methaniden)

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WO1999007676A1 true WO1999007676A1 (fr) 1999-02-18

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WO2004072021A1 (fr) * 2003-02-14 2004-08-26 Daikin Industries, Ltd. Compose d'acide fluorosulfonique, procede de production de celui-ci et utilisation de celui-ci
US20140093783A1 (en) * 2011-06-07 2014-04-03 3M Innovative Properties Company Lithium-ion electrochemical cells including fluorocarbon electrolyte additives
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WO2003017409A2 (fr) * 2001-08-17 2003-02-27 Merck Patent Gmbh Electrolytes polymeres et leur utilisation dans des cellules galvaniques
WO2003017409A3 (fr) * 2001-08-17 2004-01-22 Merck Patent Gmbh Electrolytes polymeres et leur utilisation dans des cellules galvaniques
WO2004072021A1 (fr) * 2003-02-14 2004-08-26 Daikin Industries, Ltd. Compose d'acide fluorosulfonique, procede de production de celui-ci et utilisation de celui-ci
US7482302B2 (en) 2003-02-14 2009-01-27 Daikin Industries, Ltd. Fluorosulfonic acid compound, process for producing the same, and use thereof
US20140093783A1 (en) * 2011-06-07 2014-04-03 3M Innovative Properties Company Lithium-ion electrochemical cells including fluorocarbon electrolyte additives
US9455472B2 (en) * 2011-06-07 2016-09-27 3M Innovative Properties Company Lithium-ion electrochemical cells including fluorocarbon electrolyte additives
CN111883835A (zh) * 2020-07-24 2020-11-03 香河昆仑化学制品有限公司 一种锂离子电池非水电解液和锂离子电池
CN111883835B (zh) * 2020-07-24 2023-05-23 香河昆仑新能源材料股份有限公司 一种锂离子电池非水电解液和锂离子电池
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KR20010022605A (ko) 2001-03-26
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DE19733948A1 (de) 1999-02-11
TW438803B (en) 2001-06-07

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